Water → HCID 12901378, compound

Participants

Reaction Steps

Into a 125 ml single-necked round bottom flask fitted with a teflon coated magnetic stir bar and a reflux condenser was charged 4.45 g of sodium p-toluenesulfinate, 20 ml water, 10 ml toluene, 7 g of 75% 4-bromobutyltrimethylstannane and 0.44 g of tri-n-butylhexadecylphophonium bromide. The mixture was refluxed for 2.5 hours with rapid stirring. On cooling, the organic phase was separated, dried over anhydrous magnesium sulfate and stripped of solvent on a rotary evaporator. The oil residue was distilled two times through a short path distillation head. The second distillation afforded 3.3 g of 4-(-p-tolylsulfonyl)butyltrimethylstannane, b.p. 136°-140° C. (1× 10-3 mm Hg). The presence of both the sulfonyl and trimethyltin moieties was indicated by strong infrared absorption bands at 1315 cm-1, 1300 cm-1, 1142 cm-1 (--SO2 --) and 765 cm-1 [(CH3)3Sn--]. NMR spectroscopy showed the following:

Provenance & Evidence